Stearoyl chloride → HCID 9827780, compound

HRID 1532677Notes

Reaction equation

HRID 1532677 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[NH:16][CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21].[C:23](Cl)(=O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>ClCCl>[Cl:8][C:9]1[C:10]2[N:16]([CH2:17][CH2:18][CH2:19][N:20]([CH3:21])[CH3:22])[C:40]([CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])=[N:15][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 28904464HCID 28904464, compound

Product 1

HCID 9827780HCID 9827780, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.587 g) was added to a solution containing 3-chloro-N2-[3-(dimethylamino)propyl]-1,2-benzenediamine (1.100 g) in dichloromethane (22 ml), and then stearoyl chloride (1.610 g) was added thereto while being cooled with ice. After being stirred for 4.5 hours at room temperature, the reaction mixture was diluted with dichloromethane, washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (4.0 ml) was added to a solution containing the residue (3.451 g) in ethanol (24 ml). After being stirred for 4 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (2.95 g) was purified by silica gel column chromatography (silica gel 92 g, chloroform:methanol=1:0-100:1), thereby yielding the entitled compound (1.271 g) as pale yellow solid.

Workup

  1. temperaturewhile being cooled with ice
  2. washwashed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated
  5. additionConcentrated hydrochloric acid (4.0 ml) was added to a solution
  6. additioncontaining the residue (3.451 g) in ethanol (24 ml)
  7. stirringAfter being stirred for 4 hours at 90° C.
  8. concentrationthe reaction mixture was concentrated
  9. additionThe residue, with ethyl acetate added
  10. washwas washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  11. dry with materialdried over sodium sulfate anhydride
  12. concentrationconcentrated
  13. customThe residue (2.95 g) was purified by silica gel column chromatography (silica gel 92 g, chloroform:methanol=1:0-100:1)

Sources & evidence

ORD record
ord-bcff814bac414620bcf74eecf4b43954
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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